Organocatalytic and direct asymmetric vinylogous Michael addition of 3-cyano-4-methylcoumarins to α,β-unsaturated ketones

Tetrahedron Letters

Volumn 51, Issue 50, 2010, Pages 6637-6640

  Huang, Xiong ^a   Wen, Yi Hang ^a   Zhou, Fei Ting ^a   Chen, Ce ^a   Xu, Dong Cheng ^a   Xie, Jian Wu ^a  

^a ZHEJIANG NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

3 CYANO 4 METHYLCOUMARIN DERIVATIVE; 9 AMINO 9 DEOXYEPIQUININE; COUMARIN DERIVATIVE; ENONE; KETONE; QUININE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; ENANTIOSELECTIVITY; MICHAEL ADDITION;

EID: 78650231988     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.10.055     Document Type: Article

References (104)

1. (a) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon: Oxford, 1992
2. (b) Sibi, M.; Manyem, S. Tetrahedron 2001, 56, 8033-8061
3. (c) Christoffers, J.; Baro, A. Angew. Chem. 2003, 115, 1726
4. Angew. Chem. Int. Ed. 2003, 42, 1688-1690.
5. (d) Baltini, R.; Bosica, G.; Fiorini, D.; Palmieri, A.; Petřini, M. Chem. Rev. 2007, 107, 933.
6. For recent reviews of organocatalyzed conjugate addition reactions, see: (a) Berner, O. M.; Tedeschi, L; Enders, D. Eur. J. Org. Chem. 2002, 1877-1894
7. (b) Taylor, M. S.; Jacobsen, E. N. Angew. Chem. 2006, 118, 1550-1573
8. Angew. Chem., Int. Ed. 2006, 45, 1520-1543.
9. (c) Almasl, D.; Alonso, D. A.; Mjera, C Tetrahedron: Asymmetry 2007, 18, 299-365
10. (d) Tsogoeva, S. B. Eur. J. Org. Chem. 2007, 1701-1706
11. (e) Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471-5569
12. (f) Melchiorre, P.; Marigao, M.; Carlone, A.; Bartoli, G. Angew. Chem. 2008, 120, 6232-6265
13. Angew. Chem., Int. Ed. 2008, 47. 6138.
14. (g) Bertelsen, S.; Jargensen, K. A. Chem. Soc. Rev. 2009, 38, 2178-2189.
15. Examples of chiral Lewis acid catalyzed Michael additions, see: (a) Myers, J. K.; Jacobsen, E. NJ. Am. Chem. Soc. 1999, 121, 8959-8960
16. (b) Harada, S.; Kumagai, N.; Kinoshita, T.; Matsunaga, S.; Shibasaki, M.J. Am. Chem. Soc. 2003, 125, 2580-2582
17. (c) Shintani, R.; Ueyama, K.; Yamada, I.; Hayashi, T. Org. Lett. 2004, 6, 3425
18. (d) Shintani, R.; Duan, W.-L.; Nagano, T.; Okada, A; Hayashi, T. Angew. Chem. 2005, 117, 4687-4690
19. Angew. Chem., Int. Ed. 2005, 44, 4611-4614
20. (e) Shintani, R.; Duan, W.-L; Hayashi, T. J. Am. Chem. Soc. 2006, 128, 5628-5629.
21. Examples of organocatalyzed conjugate addition reactions: (a) Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975-2978
22. (b) Gryko, D. Tetrahedron: Asymmetry 2005, 16, 1377-1383
23. (c)Yamaguchi, M.; Shiraishi, T.; Hirama, M. A. Angew. Chem., Int. Ed. 1993, 32, 1176-1178
24. (d) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520-3530
25. (e) Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Reddy, R.; Hirama, M. Tetrahedron 1997, 53, 11223-11236
26. (f) Chi, Y.; Gellmann, S. H. Org. Lett. 2005, 7, 4253-4256
27. (g) Halland, N.; Aburel, P. S.; Jargensen, K. A Angew. Chem., Int. Ed. 2003, 42, 661-665
28. (h) Halland, N.; Hansen, T.; Jargensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 4955-4957
29. (i) Pulkkinen, J.; Aburel, P. S.; Halland, N.; Jargensen, K. A. Adv. Synth. Catal. 2004, 346, 1077-1080
30. (j) Halland, N.; Aburel, P. S.; Jargensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 1270-1272
31. (k) Peelen, T.J.; Chi, Y.; Gellman, S. H. J. Am. Chem. Soc. 2005, 127, 11598-11599
32. Li, H.; Zu, L.; Wang, W.; Wang, J. Tetrahedron Lett. 2006, 47, 3145-3148
33. (l) Li, H.; Wang, J.; Zu, L; Wang, W. Tetrahedron Lett. 2006, 47, 2585-2589
34. (n) Wu, F.; Li, H.; Hong, R.; Deng, L. Angew. Chem. 2006, 118, 961-964
35. Angew. Chem., Int. Ed. 2006, 45, 947-950.
36. (o) Wang, J.; Li, H.; Zu, L.; Jiang, W.; Xie, H.; Duan, W.; Wang, W.J. Am. Chem. Soc. 2006, 128, 12652-12653
37. (p) Kim, H.; Yen, C.; Preston, P.; Chin, J. Org. Lett. 2006, 8, 5239-5242
38. (q) Albrecht, B.; Richter, C.; Vila, H.; Krawczyk; Jargensen, K. A. Chem. Eur. J. 2009, 15, 3093-3102
39. (r) Andersen, N. R.; Hansen, C.; Bertelsen, S.; Jargensena, K. A. Adv. Synth. Catal 2009, 351, 3193-3198.
40. (a) Johnson, J. R. Org. React. 1942, 210-265
41. (b) Shriller, R. L. Org. React. 1942, 1, 1-37
42. (c) Sugino, T.; Tanaka, K. Chem. Lett. 2001, 513-515
43. (d) Brufola, C.; Fringuelli, F.; Piermattl, O.; Pizzo, F. Heterocycles 1996, 43, 1257-1266
44. (e) Yavari, I.; Hekmat-Shoar, R.; Zonouzl, A. Tetrahedron Lett. 1998, 39, 2391-2392;
45. (f) Dittmer, D. C.; Li, Q.; Avilov, D. V. J. Org. Chem. 2005, 70, 4682-4686
46. (g) Alexander, V. M.; Bhat, R. P.; Samant, S. D. Tetrahedron Lett. 2005, 46, 6957-6959
47. (h) Jia, C.; Piao, D.; Kltamura, T.; Fujiwara, Y. J. Org. Chem. 2000, 65, 7516-7522
48. (i) Selles, P.; Mueller, U. Org. Lett. 2004, 6, 277-279
49. (j) Li, K.; Zeng, Y.; Neuenswander, B.; Tunge, J. A. J. Org. Chem. 2005, 70, 6515-6518
50. (k) Aoki, S.; Amamoto, C.; Oyamada, J.; Kltamura, T. Tetrahedron 2005, 61, 9291-9297.
51. Macloed, A M.; Grimwood, S.; Barton, C.; Bristow, L.; Saywell, K.; Marshall, G. R.; Ball, G. J. Med. Chem. 1995, 38, 2234-2239.
52. (a) Kennedy, R. O.; Thames, R. D. In Coumarins: Biology Application and Mode of Action; John Wiley and Sons: Chichester, 1997
53. (b) Murray, R. D. H.; Mendez, J.; Brown, S. A. In The Natural Coumarins: Occurrence, Chemistry and Biochemistry; John Wiley and Sons: New York, 1982.
54. For a recent review on vinylogous reactions, see: (a) Denmark, S. E.; Heemstra, J. J. R.; Beutner, G. L. Angew. Chem., Int. Ed. 2005, 44, 4682-4698
55. (b) Cul, H.-L.; Chen, Y.-C. Chem. Commun 2009, 4479-4486.
56. (a) Jiang, L; Zheng, H.-T.; Liu, T.-Y.; Yue, L.; Chen, Y.-C. Tetrahedron 2007, 63, 5123-5128
57. (b) Alemán, J.; Jacobsen, C. B.; Frisch, K.; Overgaard, J.; Jargensen, K. A. Chem. Commun. 2008, 632-634
58. (c) Lu, J.; Zhou, W.-J.; Liu, F.; Loh, T.-P. Adv. Synth. Catal. 2008, 350, 1796-1800
59. (d) Wang, X.-S.; Zhang, M.-M.; Li., Q.; Yao, C.-S.; Tu, S.-J. Tetrahedron 2007, 63, 5265-5273
60. (e)Xue, D.; Chen, Y.-C.; Cun, L.F.; Wang, Q-W.; zhu, J.; Deng, J.-G. Org. Lett. 2005, 7, 5293-5296
61. (f) Xie, J.-W.; Yue, L.; Xue, D.; Ma, X.-L.; Chen, Y.-C.; Wu, Y.; Zhu, J.; Deng, J.-G. Chem. Commun. 2006, 1563-1565
62. (g) Poulsen, T. B.; Bell, M.; Jargensen, K. A. Org. Biomol Chem. 2006, 4, 63-70
63. (h) Poulsen, T. B.; Alemparte, C.; Jargensen, K. A. J. Am. Chem. Soc. 2005, 127, 11614-11615
64. (i) Feng, X.; Cui, H.-L.; Xu, S.; Wu, L.; Chen, Y.-C. Chem. Eur. J. 2010. doi:10.1002/chem.201001350.
65. For selected reviews on amine/acid or amino acid catalysts, see: (a) Dalko, P. L.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726-3748
66. (b) Dalko, P. L.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138-5175
67. (c) List, B. Chem. Commun. 2006, 819-824
68. (d) Palomo, C.; Mielgo, A. Angew. Chem., Int. Ed. 2006, 45, 7876-7880
69. (e) Marcelli, T.; van Maarseveen, J. H.; Hiemstra, H. Angew. Chem., Int. Ed. 2006, 45, 7496-7504
70. (f) Xu, L W.; Luo, J.; Lu, Y. Chem. Commun. 2009, 1807-1821
71. (g) Chen, Y.-C. Synlett 2008, 1919-1930.
72. (a) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III Angew. Chem., Int. Ed. 2003, 42, 4233-4237
73. (b) Ramachary, D. B.; Chowdari, N. S.; Barbas, C F., III Synlett 2003, 1910-1914
74. (c) Ramachary, D. B.; Anebouselvy, K.; Chowdari, N. S., ; Barbas, C F., III. Org. Chem. 2004, 69, 5838-5849
75. (d) Ramachaiy, D. B.; Barbas, C F., III Org. Lett. 2005, 7, 1577-1580
76. (e) Ramachaiy, D. B.; Reddy, Y. V.; Prakash, B. V. Org. Biomol Chem. 2008, 6, 719-726.
77. (a) Ramachary, D. B.; Kishor, M.; Babul Reddy, G. Org. Biomol. Chem. 2006, 4, 1641-1646
78. (b) Ramachary, D. B.; Kishor, M. J. Org. Chem. 2007, 72, 5056-5068
79. (c) Ramachary, D. B.; Ramakumar, K.; Narayana, V. V. J. Org. Chem. 2007, 72, 1458-1463
80. (d) Ramachary, D. B.; Kishor, M. Org. Biomol. Chem. 2008, 6, 4176-4187
81. (e) Ramachary, D. B.; Reddy, Y. V.; Kishor, M. Org Biomol. Chem. 2008, 6, 4188-4197
82. (f) Ramachary, D. B.; Kishor, M.; Ramakumar, K. Tetrahedron Lett. 2006, 47, 651-656.
83. (a) Ramachary, D. B.; Barbas, C F., III Chem. Eur. J. 2004, 10, 5323-5331
84. (b) Ramachary, D. B.; Babul Reddy, G. Org. Biomol. Chem. 2006, 4, 4463-4468
85. (c) Ramachary, D. B.; Kishor, M.; Reddy, Y. V. Eur J. Org. Chem. 2008, 975-998.
86. (a) Xie, J.-W.; Chen, W.; Li, R.; Zeng, M.; Du, W.; Yue, L; Chen, Y.-C.; Wu, Y.; Zhu, J.; Deng, J.-G. Angew. Chem., Int. Ed. 2007, 46, 389-392
87. (b) Xie, J.-W.; Yue, L.; Chen, W.; Du, W.; Zhu, J.; Deng, J.-G.; Chen, Y.-C. Org. Lett. 2007, 9, 413-415
88. (c) Kang, T.-R.; Xie, J.-W.; Du, W.; Feng, X.; Chen, Y.-C. Org .Biomol Chem. 2008, 2673-2675
89. (d) Xie, J.-W.; Huang, X.; Fan, L.-P.; Xu, D.-C; Li, X.-S.; Su, H.; Wen, Y.-H. Adv. Synth. Catal. 2009, 351, 3077-3082.
90. (a) Chen, W.; Du, W.; Duan, Y.-Z.; Wu, Y.; Yang, S.-Y.; Chen, Y.-C. Angew. Chem., Int. Ed. 2007, 46, 7667-7670
91. (b) McCooey, S. H.; Connon, S.J. Org. Lett. 2007, 9, 599-602
92. (c) Ricci, P.; Carlone, A.; Bartoli, G.; Bosco, M.; Sambri, L.; Melchiorrea, P. Adv. Synth. Catal. 2008, 350, 49-53
93. (d) Tan, B.; Chua, P. J.; Zeng, X. F.; Lu, M.; Zhong, G. F. Org. Lett. 2008, 10, 3489-3492
94. (e) Lv, J.; Zhang, J. M.; Lin, Z.; Wang, Y. M. Chem. Eur. J. 2009, 15, 972-979
95. (f) Zhou, J.; Wakchaure, V.; Kraft, P.; List, B. Angew. Chem., Int. Ed. 2008, 47, 7656-7658.
96. (a) Li, X.-F.; Cun, L-F.; Lian, C-X.; Zhong, L.; Chen, Y.-C; Liao, J.; Zhu, J.; Deng, J.G. Org. Biomol. Chem. 2008, 349-353
97. (b) Lu, X. J.; Deng, L. Angew. Chem., Int. Ed. 2008, 47, 7710-7713
98. (c) Reisinger, C. M.; Wang, X.; List, B. Angew. Chem., Int. Ed. 2008, 47, 8112-8115
99. (d) Wang, X. W.; Reisinger, C. M.; List, B. J. Am. Chem. Soc. 2008, 130, 6070-6071
100. (e) Lu, X. J.; Liu, Y.; Sun, B. F.; Cindric, B.; Deng, L. J. Am. Chem. Soc. 2008, 130, 8134-8135
101. (f) Mei, K.; Jin, M.; Zhang, S.-L.; Li, P.; Liu, W.-J.; Chen, X.-B.; Xue, F.; Duan, W.-H.; Wang, W. Org. Lett. 2009, 11, 2864-2867
102. (g) Zhu, Q.; Lu, Y.-X. Chem. Commun. 2010, 46, 2235.
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